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Reactions of the N-isopropyl-α-chloroketimines with PIV dithioacids

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Abstract

A primary iminium salt formed in the reaction of PIV dithioacids with N-isopropyl-α-chloroketimines is transformed into products of nucleophilic substitution of the chlorine atom by dithiophosphorus group (SN pathway), if the imine carbon atom is bonded to the donor and small-volume methyl group, or undergoes reduction of the CCl bond (C-Cl→C-H) (Red pathway), when it is bonded with the bulky acceptor phenyl group. The same effect of substituents was discovered, when replacing methyl group with phenyl one in the position 2 of N-tert-butyl-2-chloraldimines: SN: Red ratio is 1: 0 in the case of Me and 1: 9 in the case of Ph. The iminium salts were transformed into new type ketones containing a phosphor functionality.

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Authors and Affiliations

  1. Kazan National Research Technological University, 68 ul. K. Marxa, 420015, Kazan, Russian Federation

    M. B. Gazizov, R. A. Khairullin, Yu. S. Kirillina, S. Yu. Ivanova, Kh. R. Khayarov & O. D. Khairullina

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  1. M. B. Gazizov
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  2. R. A. Khairullin
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  3. Yu. S. Kirillina
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  4. S. Yu. Ivanova
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  5. Kh. R. Khayarov
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  6. O. D. Khairullina
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Correspondence to M. B. Gazizov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2241–2245, December, 2018.

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Gazizov, M.B., Khairullin, R.A., Kirillina, Y.S. et al. Reactions of the N-isopropyl-α-chloroketimines with PIV dithioacids. Russ Chem Bull 67, 2241–2245 (2018). https://doi.org/10.1007/s11172-018-2362-6

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  • DOI: https://doi.org/10.1007/s11172-018-2362-6

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